Small Business AI Readiness Checklist

A structured assessment to evaluate whether your business is ready for AI automation — and where to start.

Before investing in AI, you need an honest picture of where your business stands. This checklist covers five key areas. Score yourself in each, and by the end you'll know exactly how ready you are.

Section 1: Current Tech Stack (___/6)

AI assistants connect to your existing tools. The more digital your operations, the faster you'll see results.

Email is on a business platform — Gmail Workspace, Microsoft 365 (not personal email)

Calendar is digital — Google Calendar, Outlook (not paper or whiteboard)

Customer/lead data is in a system — CRM, spreadsheet, or database (not sticky notes)

Invoicing is digital — QuickBooks, Xero, FreshBooks (not handwritten)

Team communicates digitally — Slack, Teams, or email (not just phone calls)

You have admin access to your tools — can add integrations, API keys, or users

5-6: Excellent foundation. 3-4: Good, minor gaps. 0-2: Digitize some basics first.

Section 2: Workflow Documentation (___/5)

AI is only as good as the instructions it receives. Processes that live in someone's head need to be written down.

You can describe your top 3 admin tasks step-by-step — not just "handle emails" but actual steps

You know who does each task today — a specific person, not "whoever gets to it"

You know how long each task takes — rough estimates count

You can identify repetitive vs. judgment-heavy tasks

There are clear rules for common scenarios — "if client asks X, we do Y"

4-5: Process-minded, great. 2-3: Workable with some effort. 0-1: Document your top 3 workflows first.

Section 3: Data Readiness (___/5)

AI needs accessible, reasonably organized data. Not perfect — just findable.

Customer/lead info is in one place — not scattered across email, napkins, and texts

Historical communications are accessible — searchable inbox, not deleted

Financial records are current — books up to date within 30 days

You have templates for common communications

Data privacy requirements are identified — HIPAA, SOC2, etc.

4-5: Data ready. 2-3: Some cleanup needed. 0-1: Organize data before AI.

Section 4: Team Readiness (___/5)

AI adoption fails without team buy-in.

Leadership is committed — willing to invest time and budget, not just curious

There's a clear internal champion — someone who will own the rollout

Team is open to changing workflows — not "we've always done it this way"

Expectations are realistic — AI assists humans, doesn't replace all judgment

Time available for onboarding — 2-4 hours in the first week

4-5: Team ready. 2-3: Some change management needed. 0-1: Address alignment first.

Section 5: Budget & Timeline (___/5)

You've calculated your current admin overhead — salaries, hours, opportunity cost

You have a budget range in mind — even rough ($3.5K, $5K, $10K+)

You understand this is a build, not a subscription — upfront investment with ongoing savings

You have a realistic timeline — 2-6 weeks for initial build

You can identify how you'll measure ROI — hours saved, leads converted, costs reduced

4-5: Budget-ready. 2-3: Needs financial planning. 0-1: Do the ROI math first.

Your Overall Score

Add your section scores:

Tech: ___/6 + Workflows: ___/5 + Data: ___/5 + Team: ___/5 + Budget: ___/5 = ___/26

22-26: Ready. You have the foundation. You'll see fast results. Book a call.

15-21: Almost There. Solid base with a few gaps. Most can be addressed during onboarding.

8-14: Getting Started. Focus on digitizing tools and documenting workflows first.

0-7: Foundation First. Get basics in place. Revisit AI in 3-6 months.

Next Steps

Document your top 3 time-consuming admin tasks — each step, who does it, how long.
List every tool your business uses — email, calendar, CRM, accounting, industry-specific.
Calculate your admin cost — use our ROI Calculator.
Talk to us — a free 30-minute call to review your results and get honest recommendations.

Ready to Talk?

Book a free 30-minute discovery call. No pressure, just honest advice.

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